Pros

Pro

Large number of applications/utilities available

Chocolatey has a massive community package repository of installs (more than 4,000 packages), and its open nature allows everyone to contribute more as needed.

Pro

No crapware

Installs silently without crapware.

Pro

Scriptable

You can put Chocolatey install commands into your powershell scripts.

Pro

Free and open source

It's licensed under Apache License 2.0 with source code available on GitHub.

Pro

Straightforward install process

To install Chocolatey simply copy the text from their site and paste it into either cmd.exe or powershell.

Pro

Upgrade all software with one command

choco upgrade all is like Windows Update for all of your 3rd party software.

Pro

Easy to use

Just open powershell and type choco install firefox to install Firefox, or choco install java to install Java.

Pro

Downloaded files are verified by checksums

Chocolatey requires checksums by default for files downloaded over non-secure locations and highly recommends it for HTTPS/SSL locations. It is moving towards requiring checkums by default for downloading from secure locations.

Pro

Manages the entire software lifecycle

From install to upgrade to uninstall, Chocolatey manages the whole process.

Pro

Builds on technologies you know

Unattended installation and PowerShell.

Pro

GUI available

There's a package, called ChocolateyGUI that can be installed and lets you use Chocolatey with a UI frontend.

Pro

Decentralized package sources

Packages can be installed from multiple sources, including private sources.

Pro

Support and features available for organizations

There is a business edition available for organizations that need more support. The business edition also includes a Package Synchronizer, Package Internalizer, Package Builder, and a host of other features.

Cons

Con

Some package installs aren't good or polished or don't install well.

Con

Unable to easily change your install directory in the free version

In the free version you must know the native installer switches and pass them through with install args. In the paid versions you have a ubiquitous install directory option where Chocolatey determines how to properly pass that to the underlying native installer.

Con

Sometimes hard to know which package to install from community package repository

The community repository contains multiple packages with similar names, making it hard to know which one to install. This is of course only related to using Chocolatey with the community repository, and you can look up the number of downloads to see which are the most widely used.